Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors
The objective of the research was to synthesise new photo switchable photochromic fluorescence compounds. Starting from N-butyl-4-bromo-3-iodo-1,8-naphthalimide new compounds: 3,4-Bis(2-phenyl-5-methyl-4-thiazolyl)-N-butyl-1,8-naphthalimide 1O and 3,4-Bis(3,5-dimethyl-4-isoxazolyl)-N-butyl-1,8-napht...
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| Format: | Article |
| Language: | English |
| Published: |
Turkish Chemical Society
2017-03-01
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| Series: | Journal of the Turkish Chemical Society, Section A: Chemistry |
| Subjects: | |
| Online Access: | http://dergipark.gov.tr/jotcsa/issue/27167/296370?publisher=turchemsoc |
| _version_ | 1797917896833236992 |
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| author | Ersin ORHAN |
| author_facet | Ersin ORHAN |
| author_sort | Ersin ORHAN |
| collection | DOAJ |
| description | The objective of the research was to synthesise new
photo switchable photochromic fluorescence compounds. Starting from N-butyl-4-bromo-3-iodo-1,8-naphthalimide
new
compounds:
3,4-Bis(2-phenyl-5-methyl-4-thiazolyl)-N-butyl-1,8-naphthalimide 1O and 3,4-Bis(3,5-dimethyl-4-isoxazolyl)-N-butyl-1,8-naphthalimide
2O were prepared via two step Suzuki
coupling reaction of aryl boronic acid and esters, and their photochromic
fluorescence properties were investigated. Although all prepared bisaryl
naphthlimides were fluorescence due to the naphthlimide moiety, among them photochrome 1O
displayed photochromism. On exposure to ultraviolet light, the photochrome 1O showed a pale yellow to blue-green
colour change due to the formation of ring closed form 1C, which reversed to the ring opened form 1O on exposure to visible light. Conversion ratio and quantum
efficiency (from O to C form) for 1O
were also determined.
Additionally,
a solvent effect on the fluorescence properties of 1O and 2O was
investigated. Increase of solvent polarity results in a red shift (to longer
wavelengths) of the fluorescence emissions. |
| first_indexed | 2024-04-10T13:20:41Z |
| format | Article |
| id | doaj.art-cbf6a8f1ccf84c31ab2e03321ca0754d |
| institution | Directory Open Access Journal |
| issn | 2149-0120 |
| language | English |
| last_indexed | 2024-04-10T13:20:41Z |
| publishDate | 2017-03-01 |
| publisher | Turkish Chemical Society |
| record_format | Article |
| series | Journal of the Turkish Chemical Society, Section A: Chemistry |
| spelling | doaj.art-cbf6a8f1ccf84c31ab2e03321ca0754d2023-02-15T16:12:04ZengTurkish Chemical SocietyJournal of the Turkish Chemical Society, Section A: Chemistry2149-01202017-03-014250151610.18596/jotcsa.296370182Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence BehaviorsErsin ORHANThe objective of the research was to synthesise new photo switchable photochromic fluorescence compounds. Starting from N-butyl-4-bromo-3-iodo-1,8-naphthalimide new compounds: 3,4-Bis(2-phenyl-5-methyl-4-thiazolyl)-N-butyl-1,8-naphthalimide 1O and 3,4-Bis(3,5-dimethyl-4-isoxazolyl)-N-butyl-1,8-naphthalimide 2O were prepared via two step Suzuki coupling reaction of aryl boronic acid and esters, and their photochromic fluorescence properties were investigated. Although all prepared bisaryl naphthlimides were fluorescence due to the naphthlimide moiety, among them photochrome 1O displayed photochromism. On exposure to ultraviolet light, the photochrome 1O showed a pale yellow to blue-green colour change due to the formation of ring closed form 1C, which reversed to the ring opened form 1O on exposure to visible light. Conversion ratio and quantum efficiency (from O to C form) for 1O were also determined. Additionally, a solvent effect on the fluorescence properties of 1O and 2O was investigated. Increase of solvent polarity results in a red shift (to longer wavelengths) of the fluorescence emissions.http://dergipark.gov.tr/jotcsa/issue/27167/296370?publisher=turchemsocPhotochromismFluorescenceDiaryletheneNaphthalimide |
| spellingShingle | Ersin ORHAN Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors Journal of the Turkish Chemical Society, Section A: Chemistry Photochromism Fluorescence Diarylethene Naphthalimide |
| title | Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors |
| title_full | Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors |
| title_fullStr | Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors |
| title_full_unstemmed | Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors |
| title_short | Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors |
| title_sort | synthesis of novel diarylethenes bearing naphthalimide moiety and photochromic fluorescence behaviors |
| topic | Photochromism Fluorescence Diarylethene Naphthalimide |
| url | http://dergipark.gov.tr/jotcsa/issue/27167/296370?publisher=turchemsoc |
| work_keys_str_mv | AT ersinorhan synthesisofnoveldiarylethenesbearingnaphthalimidemoietyandphotochromicfluorescencebehaviors |